AU2009264385B2 - Method for producing substituted biphenyls - Google Patents
Method for producing substituted biphenyls Download PDFInfo
- Publication number
- AU2009264385B2 AU2009264385B2 AU2009264385A AU2009264385A AU2009264385B2 AU 2009264385 B2 AU2009264385 B2 AU 2009264385B2 AU 2009264385 A AU2009264385 A AU 2009264385A AU 2009264385 A AU2009264385 A AU 2009264385A AU 2009264385 B2 AU2009264385 B2 AU 2009264385B2
- Authority
- AU
- Australia
- Prior art keywords
- process according
- halogen
- nitrobiphenyl
- formula
- dichloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 235000010290 biphenyl Nutrition 0.000 title claims abstract description 14
- 150000004074 biphenyls Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- 239000003446 ligand Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052763 palladium Inorganic materials 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 12
- LFADBBPCVQXYLW-UHFFFAOYSA-N 1,2,3-trifluoro-5-(2-nitrophenyl)benzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 LFADBBPCVQXYLW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- VIGVRXYWWFPORY-UHFFFAOYSA-N diphenylborinic acid Chemical compound C=1C=CC=CC=1B(O)C1=CC=CC=C1 VIGVRXYWWFPORY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- AKRFYNFPWORWIQ-UHFFFAOYSA-N 1,2-dichloro-4-(2-nitrophenyl)benzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 AKRFYNFPWORWIQ-UHFFFAOYSA-N 0.000 claims description 3
- OAIKQKOEXPBKET-UHFFFAOYSA-N 1,2-difluoro-4-(2-nitrophenyl)benzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(F)C(F)=C1 OAIKQKOEXPBKET-UHFFFAOYSA-N 0.000 claims description 3
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims description 3
- HBIJOUVSXYDCLN-UHFFFAOYSA-N 2,4-dichloro-1-(2-nitrophenyl)benzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(Cl)C=C1Cl HBIJOUVSXYDCLN-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000005171 halobenzenes Chemical class 0.000 claims description 3
- SWXPBEIQTOLKME-UHFFFAOYSA-N 2-(3,4,5-trichlorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1 SWXPBEIQTOLKME-UHFFFAOYSA-N 0.000 claims description 2
- LRWMKMWVIYXNND-UHFFFAOYSA-N 2-(3,5-dichloro-4-fluorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC(Cl)=C(F)C(Cl)=C1 LRWMKMWVIYXNND-UHFFFAOYSA-N 0.000 claims description 2
- GGHKUMDZVILSMH-UHFFFAOYSA-N 2-(3-chloro-4,5-difluorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC(F)=C(F)C(Cl)=C1 GGHKUMDZVILSMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- FJACHRXXIHYHRZ-UHFFFAOYSA-N 2-(3-fluorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC=CC(F)=C1 FJACHRXXIHYHRZ-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- -1 aromatic boronic acids Chemical class 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- UHDDEIOYXFXNNJ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)boronic acid Chemical compound OB(O)C1=CC(F)=C(F)C(F)=C1 UHDDEIOYXFXNNJ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- UWMSQOIGCCXEPJ-UHFFFAOYSA-N [(3-diphenylphosphoryl-2,2-dimethylpropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C)(C)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 UWMSQOIGCCXEPJ-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000007938 chlorocyclic compounds Chemical class 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PEDHEUQKKAVLBE-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-ethylhexyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(CC)(CCCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PEDHEUQKKAVLBE-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- UYANAUSDHIFLFQ-UHFFFAOYSA-N borinic acid Chemical class OB UYANAUSDHIFLFQ-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002940 palladium Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- HKJCELUUIFFSIN-UHFFFAOYSA-N 5-bromo-1,2,3-trifluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1F HKJCELUUIFFSIN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WUHFTNFXBQUQGP-UHFFFAOYSA-N [3-diphenylphosphorylpropyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)CCCP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 WUHFTNFXBQUQGP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- GWTHXBKWWDYAQS-UHFFFAOYSA-N 1,2-bis(diethylphosphoryl)ethane Chemical compound CCP(=O)(CC)CCP(=O)(CC)CC GWTHXBKWWDYAQS-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- FXODUJNDGCJNHJ-UHFFFAOYSA-N 2-(3,4-dichloro-5-fluorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC(F)=C(Cl)C(Cl)=C1 FXODUJNDGCJNHJ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- KBMDBLCFKPRPOC-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoro-2-(trifluoromethyl)propanenitrile Chemical compound FC(F)(F)C(Br)(C#N)C(F)(F)F KBMDBLCFKPRPOC-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- BSOPUYXMZHLZLK-UHFFFAOYSA-N [(1-diphenylphosphorylcyclobutyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(C1(CCC1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 BSOPUYXMZHLZLK-UHFFFAOYSA-N 0.000 description 1
- HEOOIMSZKJUJQT-UHFFFAOYSA-N [(1-diphenylphosphorylcyclohexyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(C1(CCCCC1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 HEOOIMSZKJUJQT-UHFFFAOYSA-N 0.000 description 1
- JIBOCVGSODYGTE-UHFFFAOYSA-N [(1-diphenylphosphorylcyclopentyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(C1(CCCC1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 JIBOCVGSODYGTE-UHFFFAOYSA-N 0.000 description 1
- PBRUQJJWKOCQMJ-UHFFFAOYSA-N [(1-diphenylphosphorylcyclopropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(C1(CC1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 PBRUQJJWKOCQMJ-UHFFFAOYSA-N 0.000 description 1
- MDDQNPQSWLXTHE-UHFFFAOYSA-N [(2-cyclobutyl-3-diphenylphosphoryl-2-methylpropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C1CCC1)(C)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDQNPQSWLXTHE-UHFFFAOYSA-N 0.000 description 1
- KVUCGXYEDSWQAO-UHFFFAOYSA-N [(2-cyclohexyl-3-diphenylphosphoryl-2-methylpropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C1CCCCC1)(C)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 KVUCGXYEDSWQAO-UHFFFAOYSA-N 0.000 description 1
- SFRFVEKXYGKVGW-UHFFFAOYSA-N [(2-cyclopentyl-3-diphenylphosphoryl-2-methylpropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C1CCCC1)(C)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SFRFVEKXYGKVGW-UHFFFAOYSA-N 0.000 description 1
- QWMJJPDUZKEMTI-UHFFFAOYSA-N [(2-cyclopropyl-1-diphenylphosphoryl-2-methylpropyl)-phenylphosphoryl]benzene Chemical compound C1CC1C(C)(C)C(P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 QWMJJPDUZKEMTI-UHFFFAOYSA-N 0.000 description 1
- XEPSBIGDQNDBJD-UHFFFAOYSA-N [(3-diphenylphosphoryl-2-methylpropyl)-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 XEPSBIGDQNDBJD-UHFFFAOYSA-N 0.000 description 1
- YNLZBBTZWUKFDU-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-ethylpentyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(CC)(CCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 YNLZBBTZWUKFDU-UHFFFAOYSA-N 0.000 description 1
- KOSZFDSDXGIZDQ-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-methylbutyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C)(CC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 KOSZFDSDXGIZDQ-UHFFFAOYSA-N 0.000 description 1
- CVBGPZVTOYHJOL-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-methylhexyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(C)(CCCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 CVBGPZVTOYHJOL-UHFFFAOYSA-N 0.000 description 1
- KNPHKZYJTXMHGD-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-propylhexyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(CCC)(CCCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 KNPHKZYJTXMHGD-UHFFFAOYSA-N 0.000 description 1
- QYXJBWDHPIISEH-UHFFFAOYSA-N [[2-(diphenylphosphorylmethyl)-2-propylpentyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(CCC)(CCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 QYXJBWDHPIISEH-UHFFFAOYSA-N 0.000 description 1
- WTMCZUNCECJIQF-UHFFFAOYSA-N [[2-butyl-2-(diphenylphosphorylmethyl)hexyl]-phenylphosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC(CCCC)(CCCC)CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 WTMCZUNCECJIQF-UHFFFAOYSA-N 0.000 description 1
- WIRRVLAFKMVSRW-UHFFFAOYSA-N [cyclohexyl(2-dicyclohexylphosphorylethyl)phosphoryl]cyclohexane Chemical compound C1CCCCC1P(C1CCCCC1)(=O)CCP(=O)(C1CCCCC1)C1CCCCC1 WIRRVLAFKMVSRW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RTAHEAZFGGWUNI-UHFFFAOYSA-N bis(3,4,5-trifluorophenyl)borinic acid Chemical compound C=1C(F)=C(F)C(F)=CC=1B(O)C1=CC(F)=C(F)C(F)=C1 RTAHEAZFGGWUNI-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007819 coupling partner Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000004857 zone melting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08158963 | 2008-06-25 | ||
| EP08158963.2 | 2008-06-25 | ||
| PCT/EP2009/057719 WO2009156359A2 (de) | 2008-06-25 | 2009-06-22 | Verfahren zur herstellung von substituierten biphenylen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009264385A1 AU2009264385A1 (en) | 2009-12-30 |
| AU2009264385B2 true AU2009264385B2 (en) | 2013-05-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009264385A Ceased AU2009264385B2 (en) | 2008-06-25 | 2009-06-22 | Method for producing substituted biphenyls |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8461390B2 (es) |
| EP (2) | EP2303828B1 (es) |
| JP (1) | JP5481476B2 (es) |
| KR (1) | KR20110025980A (es) |
| CN (2) | CN105218378A (es) |
| AR (1) | AR074158A1 (es) |
| AU (1) | AU2009264385B2 (es) |
| BR (1) | BRPI0914221A2 (es) |
| CA (1) | CA2727075C (es) |
| EA (1) | EA023304B1 (es) |
| IL (1) | IL209691A (es) |
| MX (1) | MX2010013212A (es) |
| UA (1) | UA106723C2 (es) |
| WO (1) | WO2009156359A2 (es) |
| ZA (1) | ZA201100589B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2585436B1 (en) | 2010-06-22 | 2015-03-18 | Basf Se | Process for preparing 4-hydroxypyridines |
| CN103086842B (zh) * | 2013-02-07 | 2015-04-29 | 联化科技股份有限公司 | 3,3’,4,4’,5,5’-六氟联苯的合成方法 |
| TWI519347B (zh) | 2013-10-24 | 2016-02-01 | 財團法人工業技術研究院 | 觸媒系統及以此觸媒系統製備環碳酸酯的方法 |
| CN104529786B (zh) * | 2014-12-16 | 2019-10-11 | 上海生农生化制品股份有限公司 | 3,4,5-三氟-2’-硝基联苯的合成方法 |
| CN109563023B (zh) * | 2016-08-22 | 2022-10-28 | 巴斯夫欧洲公司 | 制备取代联苯的方法 |
| EP3583093B1 (en) * | 2017-02-14 | 2021-04-14 | Basf Se | Process for preparing substituted biphenyls |
| CN107382734A (zh) * | 2017-07-21 | 2017-11-24 | 南通嘉禾化工有限公司 | 二氯二氨合钯催化硝基氯苯的Suzuki偶联反应 |
| CN109956871B (zh) * | 2017-12-25 | 2022-03-29 | 浙江省化工研究院有限公司 | 一种3,4,5-三氟-2’-硝基联苯的制备方法 |
| CN109761820B (zh) * | 2019-01-25 | 2022-03-25 | 浙江工业大学 | 一种3′,4′,5′-三氟-[1,1′-联苯]-2-胺的化学合成方法 |
| CN109942433B (zh) * | 2019-04-11 | 2022-03-25 | 浙江工业大学 | 一种3’,4’,5’-三氟-2-氨基联苯的化学合成方法 |
| US12344586B2 (en) | 2019-07-19 | 2025-07-01 | Adama Makhteshim Ltd. | Process for the preparation of biphenylamines |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
| EP4378929A1 (en) | 2022-11-29 | 2024-06-05 | Adama Makhteshim Ltd. | Synthesis of aromatic boronic acids |
| CN116082163B (zh) * | 2023-01-06 | 2023-10-13 | 河北凡克新材料有限公司 | 一种3’,4’-二氟-2’-胺基联苯的制备方法 |
| CN120081743B (zh) * | 2025-04-30 | 2025-07-25 | 辽宁众辉生物科技有限公司 | 一种氟唑菌酰胺中间体三氟硝基联苯的合成方法 |
| CN120117989B (zh) * | 2025-05-13 | 2025-07-25 | 辽宁众辉生物科技有限公司 | 一种氟唑菌酰胺中间体3’,4’,5’-三氟-2-硝基联苯的一锅法合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4231517A1 (de) | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE4340490A1 (de) | 1992-11-27 | 1994-06-01 | Merck Patent Gmbh | Verbessertes Verfahren zur Durchführung einer Kreuzkopplungsreaktion |
| ATE209620T1 (de) | 1996-03-13 | 2001-12-15 | Basf Ag | Verfahren zur herstellung von nitrobiphenylen |
| GB9621222D0 (en) | 1996-10-11 | 1996-11-27 | Zeneca Ltd | Process |
| JP2001302605A (ja) * | 2000-04-20 | 2001-10-31 | Sumitomo Chem Co Ltd | ビフェニル化合物およびその用途 |
| DE10204390A1 (de) * | 2002-02-04 | 2003-08-14 | Bayer Cropscience Ag | Disubstituierte Thiazolylcarboxanilide |
| DE102005007160A1 (de) | 2005-02-16 | 2006-08-24 | Basf Ag | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| AR052930A1 (es) | 2005-03-02 | 2007-04-11 | Basf Ag | Procedimiento para la preparacion de bifenilos sustituidos |
| SI1888545T1 (sl) * | 2005-05-18 | 2010-11-30 | Basf Se | Anilidi tiazol karboksilične kisline |
| WO2007138089A1 (en) * | 2006-06-01 | 2007-12-06 | Basf Se | Process for preparing substituted biphenyls |
| CN100569713C (zh) * | 2007-05-15 | 2009-12-16 | 大连理工大学 | 一种联苯类化合物的制备方法 |
-
2009
- 2009-06-22 CN CN201510634377.7A patent/CN105218378A/zh active Pending
- 2009-06-22 WO PCT/EP2009/057719 patent/WO2009156359A2/de not_active Ceased
- 2009-06-22 KR KR1020117001740A patent/KR20110025980A/ko not_active Ceased
- 2009-06-22 EP EP09769208.1A patent/EP2303828B1/de active Active
- 2009-06-22 AU AU2009264385A patent/AU2009264385B2/en not_active Ceased
- 2009-06-22 JP JP2011515331A patent/JP5481476B2/ja not_active Expired - Fee Related
- 2009-06-22 EA EA201100034A patent/EA023304B1/ru not_active IP Right Cessation
- 2009-06-22 BR BRPI0914221A patent/BRPI0914221A2/pt not_active IP Right Cessation
- 2009-06-22 MX MX2010013212A patent/MX2010013212A/es active IP Right Grant
- 2009-06-22 US US13/001,070 patent/US8461390B2/en active Active
- 2009-06-22 CA CA2727075A patent/CA2727075C/en active Active
- 2009-06-22 UA UAA201100685A patent/UA106723C2/uk unknown
- 2009-06-22 CN CN2009801243188A patent/CN102076651A/zh active Pending
- 2009-06-22 EP EP13189221.8A patent/EP2700630B1/de active Active
- 2009-06-25 AR ARP090102353A patent/AR074158A1/es not_active Application Discontinuation
-
2010
- 2010-12-01 IL IL209691A patent/IL209691A/en not_active IP Right Cessation
-
2011
- 2011-01-24 ZA ZA2011/00589A patent/ZA201100589B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| SHEN, W. et al. Tetrahedron Letters (1997), 38(32), 5575-5578 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201100589B (en) | 2012-03-28 |
| KR20110025980A (ko) | 2011-03-14 |
| CA2727075C (en) | 2016-05-31 |
| MX2010013212A (es) | 2010-12-21 |
| US20110105766A1 (en) | 2011-05-05 |
| EP2303828A2 (de) | 2011-04-06 |
| EP2700630A2 (de) | 2014-02-26 |
| BRPI0914221A2 (pt) | 2019-09-24 |
| US8461390B2 (en) | 2013-06-11 |
| EA023304B1 (ru) | 2016-05-31 |
| IL209691A (en) | 2014-11-30 |
| CN105218378A (zh) | 2016-01-06 |
| WO2009156359A3 (de) | 2010-07-15 |
| EP2700630B1 (de) | 2018-03-21 |
| EP2303828B1 (de) | 2014-07-30 |
| UA106723C2 (uk) | 2014-10-10 |
| EA201100034A1 (ru) | 2011-12-30 |
| CN102076651A (zh) | 2011-05-25 |
| AR074158A1 (es) | 2010-12-29 |
| AU2009264385A1 (en) | 2009-12-30 |
| JP5481476B2 (ja) | 2014-04-23 |
| CA2727075A1 (en) | 2009-12-30 |
| IL209691A0 (en) | 2011-02-28 |
| JP2011525518A (ja) | 2011-09-22 |
| WO2009156359A2 (de) | 2009-12-30 |
| EP2700630A3 (de) | 2014-04-09 |
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